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An Unprecedented Pd‐Catalyzed Carbonylative Route to Fused Furo[3,4‐ b ]indol‐1‐ones
Author(s) -
Acerbi Alessandra,
Carfagna Carla,
Costa Mirco,
Mancuso Raffaella,
Gabriele Bartolo,
Della Ca' Nicola
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201706067
Subject(s) - annulation , moiety , catalysis , chemistry , ring (chemistry) , palladium , indole test , combinatorial chemistry , carbon monoxide , reagent , molecule , carbonylation , stereochemistry , medicinal chemistry , organic chemistry
Abstract A novel and efficient catalytic approach to functionalized furo[3,4‐ b ]indol‐1‐ones is reported. It is based on a palladium‐catalyzed sequential process involving an initial cyclization of 2‐(hydroxypropyn‐1‐yl)anilines to form the indole moiety, followed by insertion of carbon monoxide and a second annulation step to build a lactone ring. In a single transformation, two fused heterocycles and three new bonds (C−N, C−C and C−O) are generated. The present methodology gives direct access to structurally complex molecules starting from readily available reagents.